Aminothiazolomorphinans with mixed κ and μ opioid activity

J Med Chem. 2011 Mar 24;54(6):1903-13. doi: 10.1021/jm101542c. Epub 2011 Feb 25.

Abstract

A series of N-substituted and N'-substituted aminothiazole-derived morphinans (5) were synthesized for expanding the structure-activity relationships of aminothiazolo-morphinans. Although their affinities were somewhat lower than their prototype aminothiazolo-N-cyclopropylmorphinan (3), 3-aminothiazole derivatives of cyclorphan (1) containing a primary amino group displayed high affinity and selectivity at the κ and μ opioid receptors. [(35)S]GTPγS binding assays showed that the aminothiazolomorphinans were κ agonists with mixed agonist and antagonist activity at the μ opioid receptor. These novel N'-monosubstituted aminothiazole-derived morphinans may be valuable for the development of drug abuse medications.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Humans
  • Morphinans / chemical synthesis*
  • Morphinans / chemistry
  • Morphinans / pharmacology
  • Radioligand Assay
  • Receptors, Opioid, kappa / agonists*
  • Receptors, Opioid, mu / agonists*
  • Receptors, Opioid, mu / antagonists & inhibitors*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thiazoles / pharmacology

Substances

  • Morphinans
  • Receptors, Opioid, kappa
  • Receptors, Opioid, mu
  • Thiazoles